US6563004B2 - Process for preparing monoisopropylamine - Google Patents
Process for preparing monoisopropylamine Download PDFInfo
- Publication number
- US6563004B2 US6563004B2 US09/729,461 US72946100A US6563004B2 US 6563004 B2 US6563004 B2 US 6563004B2 US 72946100 A US72946100 A US 72946100A US 6563004 B2 US6563004 B2 US 6563004B2
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- United States
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- containing compounds
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- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 77
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 66
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 47
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
- 239000001301 oxygen Substances 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000010949 copper Substances 0.000 claims abstract description 23
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 22
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 18
- 239000010941 cobalt Substances 0.000 claims abstract description 18
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052802 copper Inorganic materials 0.000 claims abstract description 18
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 239000007789 gas Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 38
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 abstract description 21
- 239000000377 silicon dioxide Substances 0.000 abstract description 18
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract description 17
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract description 14
- 235000012239 silicon dioxide Nutrition 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 238000005470 impregnation Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000001556 precipitation Methods 0.000 description 11
- 239000012876 carrier material Substances 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- -1 vanadyl pyrophosphate Chemical compound 0.000 description 6
- 102100032373 Coiled-coil domain-containing protein 85B Human genes 0.000 description 5
- 101000868814 Homo sapiens Coiled-coil domain-containing protein 85B Proteins 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000000137 annealing Methods 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910001936 tantalum oxide Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 150000003755 zirconium compounds Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(II) oxide Inorganic materials [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical group [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N nickel(II) oxide Inorganic materials [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- XNHGKSMNCCTMFO-UHFFFAOYSA-D niobium(5+);oxalate Chemical compound [Nb+5].[Nb+5].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O XNHGKSMNCCTMFO-UHFFFAOYSA-D 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical class [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- OTCVAHKKMMUFAY-UHFFFAOYSA-N oxosilver Chemical class [Ag]=O OTCVAHKKMMUFAY-UHFFFAOYSA-N 0.000 description 1
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- GGROONUBGIWGGS-UHFFFAOYSA-N oxygen(2-);zirconium(4+);hydrate Chemical compound O.[O-2].[O-2].[Zr+4] GGROONUBGIWGGS-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 235000016804 zinc Nutrition 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical class [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
- 229910006587 β-Al2O3 Inorganic materials 0.000 description 1
- 229910003158 γ-Al2O3 Inorganic materials 0.000 description 1
- 229910006415 θ-Al2O3 Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
Definitions
- the present invention relates to a process for preparing monoisopropylamine (MIPA; (CH 3 ) 2 CHNH 2 ) by reacting acetone at elevated temperature and elevated pressure with ammonia and with hydrogen in the presence of a catalyst.
- MIPA monoisopropylamine
- MIPA is an important organic intermediate which is required inter alia as precursor for preparing crop protection agents.
- MIPA is prepared industrially by aminating hydrogenation of isopropanol or acetone with ammonia using catalysts.
- DE-A-1 543 354 discloses the synthesis of MIPA by aminating hydrogenation of acetone in the presence of cobalt catalysts.
- DT-A-1803 083, DT-A-1817 691, FR-A-159 0871, DE-A-18 03 083 and HU-A-47456 describe the preparation of MIPA by aminating hydrogenation of acetone in the presence of catalysts of the Raney nickel type.
- DL-A-75086, DE-A-17 93 220, GB-A-1218 454, CN-A-1130 621, CS-A-185 962 and CS-A-239 445 relate to the preparation of MIPA by aminating hydrogenation of acetone in the presence of nickel/aluminum oxide catalysts.
- EP-A-284 398 and CN-A-111 0629 relate to nickel catalysts doped with Ru or with Cr and Cu for preparing MIPA from acetone.
- EP-A-514 692 discloses catalysts containing copper, nickel and/or cobalt, zirconium oxide and/or aluminum oxide for the catalytic amination of alcohols in the gas phase with ammonia or primary amines and hydrogen.
- EP-A-382 049 discloses catalysts which comprise oxygen-containing zirconium, copper, cobalt and nickel compounds, and processes for the hydrogenating amination of alcohols or carbonyl compounds.
- the preferred zirconium oxide content in these catalysts is from 70 to 80% by weight (loc. cit.: page 2, last paragraph; page 3, 3 rd paragraph; Examples).
- DE-A-19 53 263 discloses the use of Co-, Ni- and Cu-containing catalysts with Al 2 O 3 or SiO 2 as carrier material for preparing amines from alcohols.
- the earlier European application no. 99111282.2 of Jun. 10, 1999 relates to a process for preparing amines by reacting primary or secondary alcohols with nitrogen compounds in the presence of catalysts comprising zirconium dioxide, copper, nickel and cobalt.
- the catalysts ought accordingly to have a high activity and a high chemical stability under the reaction conditions, and achieve the above object even on use of an only small molar excess of ammonia relative to acetone.
- MIPA monoisopropylamine
- Al 2 O 3 aluminum oxide
- ZrO 2 zirconium dioxide
- TiO 2 titanium dioxide
- SiO 2 silicon dioxide
- the catalysts employed in the process according to the invention are preferably in the form of catalysts which consist only of catalytically active mass and, where appropriate, a shaping auxiliary (such as, for example, graphite or stearic acid) if the catalyst is employed as shaped articles, that is to say contain no other catalytically inactive additives.
- a shaping auxiliary such as, for example, graphite or stearic acid
- the catalytically active mass can be introduced after grinding as powder or as chips into the reaction vessel or, preferably, after grinding, mixing with molding auxiliaries, shaping and annealing, introduced as catalyst shaped articles—for example as tablets, beads, rings, extrudates (for example strands)—into the reactor.
- concentration data (in % by weight) of the components of the catalyst are in each case based—unless stated otherwise—on the catalytically active mass of the prepared catalyst after its last heat treatment and before the treatment with hydrogen.
- the catalytically active mass of the catalyst after its last heat treatment and before the treatment with hydrogen is defined as the total of the masses of the catalytically active ingredients and the carrier materials and essentially comprises oxygen-containing compounds of aluminum, zirconium, titanium and/or silicon, oxygen-containing compounds of copper, oxygen-containing compounds of nickel and oxygen-containing compounds of cobalt.
- the total of the abovementioned catalytically active ingredients and of the abovementioned carrier materials in the catalytically active mass is normally from 70 to 100% by weight, preferably from 80 to 100% by weight, particularly preferably from 90 to 100% by weight, in particular from 95 to 100% by weight, very especially 100% by weight.
- the catalytically active mass of the catalysts employed in the process according to the invention may further comprise one or more elements (oxidation state 0) or their inorganic or organic compounds selected from groups I A to VI A and I B to VII B and VIII of the Periodic Table.
- transition metals such as Mn or manganese oxides, Re or rhenium oxides, Cr or chromium oxides, Mo or molybdenum oxides, W or tungsten oxides, Ta or tantalum oxides, Nb or niobium oxides or niobium oxalate, V or vanadium oxides or vanadyl pyrophosphate, zinc or zinc oxides, silver or silver oxides, lanthanides such as Ce or CeO 2 or Pr or Pr 2 O 3 , alkali metal oxides such as Na 2 O, alkali metal carbonates such as Na 2 CO 3 and K 2 CO 3 , alkaline earth metal oxides such as SrO, alkaline earth metal carbonates such as MgCO 3 , CaCO 3 , BaCO 3 , phosphoric anhydrides and boron oxide (B 2 O 3 ).
- transition metals such as Mn or manganese oxides, Re or rhenium oxides, Cr or chromium oxides, Mo or
- the catalytically active mass of the catalysts employed in the process according to the invention comprises, after preparation thereof and before the treatment with hydrogen,
- Al 2 O 3 aluminum oxide
- ZrO 2 zirconium dioxide
- TiO 2 titanium dioxide
- SiO 2 silicon dioxide
- the catalytically active mass of very particularly preferably employed catalysts comprises, after preparation thereof and before the treatment with hydrogen,
- Al 2 O 3 aluminum oxide
- SiO 2 silicon dioxide
- the ratio by weight of cobalt to nickel, in each case calculated as metal is from 4:1 to 1:4, particularly preferably from 2:1 to 1:2.
- the ratio by weight of (cobalt and nickel) to copper, in each case calculated as metal is from 3:1 to 20:1, particularly preferably from 3:1 to 10:1.
- Catalysts preferably employed in the process according to the invention contain no catalytically active amounts of V, Nb, Ta, Cr, Mo, W, Mn and/or Re and/or their inorganic or organic compounds.
- catalysts preferably employed contain no catalytically active amounts of Fe, Ru, Rh, Pd, Os, Ir, Pt, Ag and/or Au and/or their inorganic or organic compounds.
- catalysts preferably employed contain no catalytically active amounts of Zn, In and/or Sn and/or their inorganic or organic compounds.
- the catalysts can be obtained, for example, by peptizing powdered mixtures of the hydroxides, carbonates, oxides and/or other salts of the components with water and subsequently extruding and annealing (heat-treating) the resulting composition.
- precipitation methods are generally used to prepare the catalysts according to the invention.
- they can be obtained, for example, by joint precipitation of the nickel, cobalt and copper components from an aqueous salt solution containing these elements using mineral bases in the presence of a slurry or suspension of fine-particle powders of an oxygen-containing aluminum, silicon, titanium and/or zirconium compound of low solubility, and subsequently washing, drying and calcining the resulting precipitate.
- oxygen-containing aluminum, silicon, titanium and zirconium compounds of low solubility which may be used are aluminum oxide, aluminum oxide hydrate, silicon dioxide, titanium dioxide, zirconium dioxide, zirconium oxide hydrate, zirconium phosphates, borates and silicates.
- the catalysts used in the process according to the invention are advantageously prepared by joint precipitation (mixed precipitation) of all their components. This is expediently done by adding an aqueous mineral base, in particular an alkali metal base, for example sodium carbonate, sodium hydroxide, potassium carbonate or potassium hydroxide, to a hot aqueous salt solution containing the catalyst components with stirring until the precipitation is complete.
- an aqueous mineral base in particular an alkali metal base, for example sodium carbonate, sodium hydroxide, potassium carbonate or potassium hydroxide
- the nature of the salts used is generally not critical: since what principally matters in this procedure is the solubility of the salts in water, one criterion for the preparation of these relatively highly concentrated salt solutions is that they necessarily have good solubility in water. It is regarded as self-evident that, in the selection of the salts of the individual components, of course the anions in the salts chosen will not result in interference, whether by causing unwanted precipitation or by impeding or preventing the
- the precipitates obtained in these precipitation reactions are generally chemically inhomogeneous and consist inter alia of mixtures of the oxides, oxide hydrates, hydroxides, carbonates and insoluble and basic salts of the metals employed. It may prove to be beneficial for the filterability of the precipitates if they are aged, i.e. if they are left alone for some time after the precipitation, where appropriate with heating or passing air through.
- the precipitates obtained by these precipitation processes are further processed to the catalysts used in the process according to the invention in a conventional way. After washing, they are generally dried at from 80 to 200° C., preferably from 100 to 150° C., and then calcined.
- the calcination (heat treatment) is generally carried out at temperatures between 300 and 800° C., preferably at from 400 to 600° C., in particular at from 450 to 550° C.
- the catalyst is expediently conditioned, whether by adjusting it to a particular particle size by grinding, or by being ground and then mixed with molding auxiliaries such as graphite or stearic acid, compressed to moldings using a tablet press, and annealed (heat-treated).
- molding auxiliaries such as graphite or stearic acid
- the annealing temperatures generally correspond to the temperatures for the calcination.
- the catalysts prepared in this way contain the catalytically active metals in the form of a mixture of their oxygen-containing compounds, i.e. in particular as oxides and mixed oxides.
- the catalysts used in the process according to the invention are preferably prepared by impregnating aluminum oxide (Al 2 O 3 ), zirconium dioxide (ZrO 2 ), titanium dioxide (TiO 2 ), silicon dioxide (SiO 2 ) or mixtures of two or more of these carrier materials which are in the form, for example, of powders, chips or shaped articles such as strands, tablets, beads or rings.
- Aluminum oxide (Al 2 O 3 ) is preferably employed in the form of ⁇ -, ⁇ -, ⁇ - or ⁇ -Al 2 O 3 or D10-10 from BASF.
- Silicon dioxide (SiO 2 ) is employed, for example, in the form of a silicon dioxide obtained by a precipitation from waterglass or by the sol-gel process, in the form of mesoporous SiO 2 , silica gel (for example as described in Ullmann, Enzykl. Techn. Chem., 4 th edition, Volume 21, pp. 457-63, 1982) or in the form of silicates such as kaolin, hectorite or aluminosilicates or alkali metal or alkaline earth metal aluminosilicates (zeolites), magnesium silicates (for example steatite), zirconium silicates, cerium silicates or calcium silicates.
- silicates such as kaolin, hectorite or aluminosilicates or alkali metal or alkaline earth metal aluminosilicates (zeolites), magnesium silicates (for example steatite), zirconium silicates, cerium
- Zirconium dioxide is employed, for example, in the monoclinic or tetragonal form, preferably in the monoclinic form, and titanium dioxide is employed, for example, as anatase or rutile.
- Aluminum oxide is very particularly preferred as carrier material in the catalysts employed in the process according to the invention.
- Shaped articles of the abovementioned carrier materials can be produced by conventional processes.
- the impregnation of these carrier materials likewise takes place by conventional processes as described, for example, in EP-A-599 180, EP-A-673 918 or A. B. Stiles, Catalyst Manufacture—Laboratory and Commercial Preparations, Marcel Dekker, pages 89 to 91, New York (1983), by application of an appropriate metal salt solution in each case in one or more impregnation stages, the metal salts used being, for example, corresponding nitrates, acetates or chlorides.
- the composition is dried (heat treatment) and, where appropriate, calcined after the impregnation.
- the impregnation can take place by the so-called incipient wetness method in which the oxidic carrier material is moistened with the impregnation solution in accordance with its water-uptake capacity until saturated and no more.
- the impregnation can also take place in supernatant solution.
- Multistage impregnation processes it is expedient to dry and, where appropriate, calcine between individual impregnation steps. Multistage impregnation is particularly advantageously applicable when a relatively large amount of metal is to be applied to the carrier material.
- the impregnation can take place simultaneously with all the metal salts or in any sequence of the individual metal salts successively.
- a special form of impregnation is represented by spray drying, in which the catalyst carrier mentioned is sprayed in a spray dryer with the component(s) to be applied in a suitable solvent.
- the advantage of this variant is the combination of application and drying of the active component(s) in one step.
- the produced catalysts can be stored as such. They are normally reduced by treatment with hydrogen before they are employed according to the invention. However, they can also be employed without this previous reduction, in which case they are reduced by the hydrogen present in the reactor under the conditions of the hydrogenating amination.
- the catalysts are generally exposed to a nitrogen/hydrogen atmosphere initially at from 150 to 200° C. over a period of from 12 to 20 hours and then treated in a hydrogen atmosphere at from 200 to 400° C. for up to about 24 hours.
- at least part of the oxygen-containing metal compounds present in the catalysts is reduced to the corresponding metals so that these are present together with the various oxygen compounds in the active form of the catalyst.
- oxygen-containing compounds of aluminum and/or manganese calculated as Al 2 O 3 and MnO 2 respectively
- the catalysts disclosed in EP-A-514 692 whose catalytically active mass comprises, before the treatment with hydrogen, from 5 to 100% by weight of an oxide of copper and nickel in the atomic ratio of from 1:1 to 10:1, preferably from 2:1 to 5:1, and zirconium oxide and/or aluminum oxide, in particular the catalysts disclosed in loc. cit. on page 3, lines 20 to 30, whose catalytically active mass comprises, before the treatment with hydrogen, from 20 to 80, in particular from 40 to 70, % by weight Al 2 O 3 and/or ZrO 2 , from 1 to 30% by weight CuO, from 1 to 30% by weight NiO and from 1 to 30% by weight CoO.
- the catalysts disclosed in DE-A-19 53 263 comprising cobalt, nickel and copper and aluminum oxide and/or silicon dioxide with a metal content of from 5 to 80% by weight, in particular from 10 to 30% by weight, based on the complete catalyst, where the catalysts comprise, calculated on the metal content, from 70 to 95% by weight of a mixture of cobalt and nickel and from 5 to 30% by weight of copper, and where the ratio by weight of cobalt to nickel is from 4:1 to 1:4, in particular from 2:1 to 1:2.
- the process according to the invention can be carried out batchwise or, preferably, continuously as follows, the catalyst preferably being disposed as fixed bed in the reactor. Flow through the catalyst bed can be either from top to bottom or from bottom to top.
- Tubular reactors are particularly suitable for the continuous process.
- the conversion of acetone into MIPA is carried out in a tube bundle reactor.
- the hydrogenating amination of acetone can be carried out in the liquid phase or in the gas phase.
- the reaction is normally carried out at temperatures of from 30 to 300° C., preferably from 50 to 250° C., in particular from 70 to 200° C.
- the reaction is generally carried out under an absolute pressure of from 1 to 300 bar (0.1 to 30 MPa). Absolute pressures of from 5 to 250 bar are preferably employed, in particular from 20 to 200 bar.
- the use of higher temperatures and a higher total pressure is possible.
- the total pressure in the reaction vessel which derives from the total of the partial pressures of ammonia, of acetone, of the products formed in the reaction and of the solvent which is also used where appropriate at the stated temperatures, is expediently adjusted to the required reaction pressure by injecting hydrogen. It is possible in this connection to use a mixture of hydrogen and an inert gas, such as, for example, nitrogen, in place of pure hydrogen.
- the hydrogen is generally fed into the reaction in an amount of from 5 to 400 l (S.T.P.), preferably in an amount of from 50 to 200 l (S.T.P.), per mole of acetone, the liter data having been converted in each case to standard conditions (S.T.P.).
- the reaction preferably takes place without additional solvent.
- a solvent which is inert under the reaction conditions such as methanol, ethanol, propanol, tetrahydrofuran, dioxane, N-methylpyrrolidone, Mihagol or ethylene glycol dimethyl ether.
- the proportion of packings in such catalyst preparations can be from 20 to 80, particularly preferably from 30 to 60 and, in particular, from 40 to 50 parts by volume.
- the procedure in practice is generally to feed the acetone and the ammonia simultaneously into the catalyst, which is preferably present in a tube bundle reactor, at the required reaction temperature and the required pressure.
- the molar ratio of acetone to ammonia is generally from 1:1 to 1:250, preferably from 1:1 to 1:50, particularly preferably from 1:1.2 to 1:10.
- the space velocity in this case is generally from 0.05 to 5, preferably from 0.05 to 2, kg of acetone per liter of catalyst (bulk volume) and per hour. It is expedient in this case for the reactants to be heated even before being fed into the reaction vessel.
- the reactants can be passed either upward or else downward through the reactor. Excess ammonia can be recycled together with the hydrogen.
- the ammonia and the hydrogen are removed therefrom, and the resulting MIPA is purified by distillation. Recovered ammonia and hydrogen are advantageously returned to the reaction zone. The same applies to any incompletely reacted acetone or isopropanol produced by hydrogenation. It is also possible to return part of the total discharge from the reactor.
- the water formed during the reaction generally has no adverse effect on the degree of conversion, the reaction rate, the selectivity and the catalyst service life and is therefore expediently removed from the reaction product only when it is worked up by distillation.
- Aluminum oxide extrudates with a strand diameter of 4 mm were covered with a solution containing 5% by weight of each of Co and Ni and 2% by weight of Cu (calculated as metal). This was a solution of the metal nitrates.
- the strands were dried at 120° C. and then annealed at 520° C.
- the resulting catalyst A had the composition:
- a high-pressure reactor with an internal diameter of 45 mm and a length of 350 cm was used.
- a thermoelement with a diameter of 12 mm was attached in the middle of the reactor in the axial direction.
- Acetone, ammonia and hydrogen were fed into the reactor from top to bottom.
- the reactor pressure was adjusted by supplying hydrogen. Downstream of the reactor, the reaction mixture was cooled, decompressed to atmospheric pressure and analyzed.
- Temperature program 50° C. for 10 min., to 150° C. at 4° C./min.
- Carrier gas nitrogen
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Applications Claiming Priority (3)
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US (1) | US6563004B2 (fr) |
EP (1) | EP1106601B1 (fr) |
JP (1) | JP2001199939A (fr) |
BR (1) | BR0005746A (fr) |
DE (1) | DE50005403D1 (fr) |
Cited By (1)
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US20040122259A1 (en) * | 2002-12-20 | 2004-06-24 | Till Gerlach | Preparation of an amine |
Families Citing this family (10)
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DE10145119A1 (de) | 2001-09-13 | 2003-04-03 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE10156685A1 (de) * | 2001-11-17 | 2003-05-28 | Basf Ag | Verfahren zur Herstellung von Monoisopropylamin |
DE10211101A1 (de) * | 2002-03-14 | 2003-09-25 | Basf Ag | Katalysatoren und Verfahren zur Herstellung von Aminen |
CN100395229C (zh) * | 2005-03-04 | 2008-06-18 | 江西盾牌化工有限公司 | 低压法合成3-戊胺的工艺 |
CN102372638A (zh) * | 2010-08-19 | 2012-03-14 | 中国石油化工股份有限公司 | 生产一异丙胺的方法 |
CN103946208B (zh) | 2011-11-21 | 2016-08-24 | 巴斯夫欧洲公司 | 制备乙基胺和单异丙基胺(mipa)的方法 |
US8766009B2 (en) | 2011-11-21 | 2014-07-01 | Basf Se | Process for preparing ethylamines and monoisopropylamine (MIPA) |
JP6143867B2 (ja) * | 2012-08-22 | 2017-06-07 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 触媒成形体を処理する方法および高められた機械的強度を有する触媒成形体 |
CN104226315B (zh) * | 2014-09-30 | 2017-01-11 | 厦门大学 | 一氧化碳加氢制混合烃的Co基催化剂及其制备方法 |
CN106397219B (zh) * | 2016-08-26 | 2018-03-27 | 安徽昊源化工集团有限公司 | 一种丙酮加氢氨化合成异丙胺的方法 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040122259A1 (en) * | 2002-12-20 | 2004-06-24 | Till Gerlach | Preparation of an amine |
US7034186B2 (en) | 2002-12-20 | 2006-04-25 | Basf Aktiengesellschaft | Preparation of an amine |
Also Published As
Publication number | Publication date |
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EP1106601B1 (fr) | 2004-02-25 |
BR0005746A (pt) | 2001-07-17 |
DE50005403D1 (de) | 2004-04-01 |
JP2001199939A (ja) | 2001-07-24 |
US20010003137A1 (en) | 2001-06-07 |
EP1106601A1 (fr) | 2001-06-13 |
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